US2931840A - Process for preparing 2, 3, 3, 3-tetrafluoropropene - Google Patents

Process for preparing 2, 3, 3, 3-tetrafluoropropene Download PDF

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US2931840A
US2931840A US776184A US77618458A US2931840A US 2931840 A US2931840 A US 2931840A US 776184 A US776184 A US 776184A US 77618458 A US77618458 A US 77618458A US 2931840 A US2931840 A US 2931840A
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mixture
tetrafluoropropene
methyl chloride
tetrafiuoroethylene
reactor
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Marquis David Maley
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EIDP Inc
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EI Du Pont de Nemours and Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons

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  • the prior art discloses two complex routes to the olefin described in the present invention.
  • 2,3,3,3-tetrafiuoropropene has been synthesized by a 6-step process starting with glyceryl trichloride involving successive chlorination, dehydrochlorination, and fluorination reactions.
  • the second method reported is a photochemical reaction of trifluoroiodomethane and 2- chloro-1,1-difiuoroethylene followed by a combination reduction and dehydrohalogenation reaction.
  • the present invention is directed to a process for preparing 2,3,3,3-tetrafluoropropene
  • the pyrolysis of a mixture of about 1 mole of methyl chloride with (a) about 1 mole of tetrafiuoroethylene or (b) about 2 moles of monochlorodifiuoromethane, said monochlorodifiuoromethane forming tetrafiuoroethylene in situ is carried out at about 700 C. to about 950 C.
  • the starting materials for this novel process are halogen-containing organic compounds.
  • the first member of the mixture is methyl chloride.
  • the second member of a mixture may be either monochlorodifluoromethane or tetrafiuoroethylene. All of these compounds are readily available.
  • the alternate mixture utilized according to the present invention consists of chlorodifiuoromcthane and methyl chloride and is operable when the molar ratio of CHClF CH Cl is within the range of greater than 1:1 to 2:1, the preferred practical range is 1.6/1 to 2.5/1 moles of chlorodifiuoromethane to methyl chloride; when this molar ratio is greater than 2:1 the effect is one of uneconomical usage of material.
  • the process of the present invention is carried out by 2.9mm Patented Apr. 5, 1960 continuously introducing the two described components. which make up the mixture, in the vapor phase into a reactor which is inert to the starting materials.
  • the reactor is maintained at a temperature from about 700 C. to about 950 C.
  • the molar ratio of the components of the mixture is maintained as discussed in the previous paragraph.
  • the reactant vapors are then converted to the desired 2,3,3,3-tetrafiuoropropene by pyrolytic action, i.e., by the action of heat.
  • a convenient form of reactor is a metal tube. However, it must be inert to the reactants. Carbon and the noble metals, particularly platinum and silver, are sufficiently inert.
  • a preferred material of construction is a platinum-lined reactor.
  • the reactor tube may be heated by conventional methods.
  • a preferred and convenient way is to place the tube in an electric furnace, which supplies the heat necessary to maintain the reaction temperature.
  • the contact times which are preferred range from 0.5 to 3 seconds. Longer contact times lead to higher molecular weight products instead of the desired 2,3,3,3- tetrafiuoropropene and also tend to carbonize the reactants such as methyl chloride and tetrafiuoroethylene. With shorter contact times, low conversion is obtained.
  • determining contact times one must consider the volume of the efiiectively heated zone of the reactor, the volume occupied by the reactants at the time they are introduced into the reactor and the rate of feeding the reactants into the reactor.
  • the volume of the effectively heated zone is determined by multiplying the effectively heated length times the cross-sectional area; and the volumes occupied by the reactants are calculated at 25? C. and 760 mm. (Hg) absolute pressure. The contact time will be controlled by the feed rate.
  • the product gases are then collected from the outlet of the reactor tube, cooled, scrubbed with water to remove the acid by-product HCl, and dried.
  • the 2,3,3,3-tetrafluoropropene may be partially separated from the reaction mixture by distillation to yield a product useful for most chemical reactions.
  • Highly purified samples may be obtained either by gas chromatographic separation or by bromination followed by debromination of the purified dibromide.
  • the operable temperature limits have been found to be from about 700 C. to about 950 C. Below 700 C., the conversion is reduced to a point where the process becomes impractical. At about 950 C. and higher, degradation of the reactants and formation of less desirable products occur.
  • the preferred range is 800 to 900 C.
  • the reactor used in Examples 1 through IV consists of a platinum-lined metal tube 6 mm. ID. x 24 inches heated in an S-inch electric furnace over an efiective reaction length of 5 inches. Analysis of the product gas streams is effected bymeans of mass spectrometry.
  • EXAMPLE V Preparation "of highly purified 2,3,3,3-'tetfafiuoropropene '
  • the reactor used consists of a platinum-lined metal tube 6 mm. ID. x 24 inches heated by two 8-inch electric furnaces. the first one serving as a preheater. The effective reaction lengthis -10 inches. Over a period of 220 minutes a mixture of'304 parts (3.04 mols) of tetrafiuoroethylene and 155parts (3.07 mols) of methyl chloride is fed to the reactor.
  • the preheater is maintained at 800 C. and the reactor at-88O C.
  • the contact time is 2.6 seconds.
  • the off gases are scrubbed free of acid by a countercurrent water scrubber, dried, and condensed in a trap cooled to 78 C.
  • This condensate weighing 242 parts, is distilled using a /2 x 3' silvered column packed with metal packing and a head equipped with magnetic takeoff.
  • the condenser is maintained at 75 C. and the distillation-is performed at a 13/2 reflux ratio. The fractions listed below-are collected.
  • Fraction B. P., C. Wt. (parts) (The lesson distillation is due to material non-condensable at --78 C.)
  • Fractions I, 11, IV and V are combined and brominated.
  • a bromination apparatus consisting of a gas washing bottle, the inlet tube having a fritted disk, is used; the'calculate'd amount of bromine is placed in thebottleand overlaid with a thin layer of water. The bromine portionis cooled in ice water while a heat lamp isfocused on the bromine-water interface. The olefins are bubbled in at such a rate that nearly complete absorption'occurs. The brominated mixture is then de-colorized with aq.
  • the 2,3,3,3-tetrafluoropropene obtained by the process of the present invention has been relatively unavailable to the present time because of the difficulty of preparing the compound.
  • the present novel process therefore yields a heretofore rare but valuable monomer.
  • This monomer may be homopolymerized.
  • the monomer is further useful in that it may be copolymerized with other unsaturated compounds such as tetrafiuoroethylene, trifiuoroethylene, vinylidene fluoride, chlorotrifluoroethylene, acrylonitrile, and '1,1,2-trifluorobutadiene-1,3 to yield plastic or elastomeric polymers.
  • a process for preparing 2,3,3,3-tetrafiuoropropene wherein a mixture of about 1 mol of'methyl chloride and a reactant taken from the group consisting of about .1 mol of tetrafiuoroethylene and about 2 moles of'monochlorodifiuoromethane ispyrolyzed, within a contact time range of 0.5 to 3.0 seconds, at a temperature within the range of about 700C. to about 950 C. to'form 2,3,3,3- tetrafiuoropropene which is then recovered from the product stream.
  • a process for preparing 2,3,3,3-tetrafluoropropene wherein a mixture of about 1 mol of methyl chloride and a reactant taken from 'the group consisting of from 0.8 to 1.25 moles of tetrafiuoroethylene and from 1.6 to 2.5 moles of monochlorodifluoromethane is pyrolyzed, within a contact time range of 0.5 to 3'seconds, at a temperature within the range of about 700 C. to about 950 C. to form 2,3,3,3-tctrafluoropropenewhich is then recovered from the product stream.
  • a process for preparing 2,3,3,3-tetrafluoropropene wherein a mixture of about 1 mol of methyl chloride and from 0.8 to 1.25 moles of tetrafiuoroethylene is pyrolyzed, within a contact time range of 0.5 to 3.0 seconds, at a temperature within the range of about 700 C. to about 950 C. to form 2,3,3,3-tetrafiuoropropene which is then recovered from the product stream.
  • Columg 1 line 67 for 12.1" read 1.-6:1

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

PROCESS FOR PREPARING 2,3,3,3-TETRA- FLUOROPROPENE David Maley Marquis, Wilmington, Del., assignor to E. I.
du Pont de Nemours and Company, Wilmington, Del., a corporation of Delaware No Drawing. Application November 25, 1958 Serial No. 776,184
4 Claims. (Cl. 260-6533) The process comprises the pyrolysis of a mixture of methyl chloride with tetrafiuoroethylene or of methyl chloride with chlorodifluoromethane, the chlorodifiuoromethane forming tetrafiuoroethylene in situ. This unique fiuoroolefin, heretofore not readily obtainable, is a valuable monomer for polymerization and copolymerization reactions.
The prior art discloses two complex routes to the olefin described in the present invention. In the first instance, 2,3,3,3-tetrafiuoropropene has been synthesized by a 6-step process starting with glyceryl trichloride involving successive chlorination, dehydrochlorination, and fluorination reactions. The second method reported is a photochemical reaction of trifluoroiodomethane and 2- chloro-1,1-difiuoroethylene followed by a combination reduction and dehydrohalogenation reaction. These processes taught by the prior art are indirect and unwieldy. 7
It is an object of the present invention to provide a novel process for the preparation of 2,3,3,3-tetrafluropropene. It is a further object of the present invention to prepare 2,3,3,3-tetrafiuoropropene by a novel process which results in increased yield and a significantly pure product not heretofore readily attainable. These and other objects will be apparent from the present specification and claims which follow.
More specifically, the present invention is directed to a process for preparing 2,3,3,3-tetrafluoropropene Wherein the pyrolysis of a mixture of about 1 mole of methyl chloride with (a) about 1 mole of tetrafiuoroethylene or (b) about 2 moles of monochlorodifiuoromethane, said monochlorodifiuoromethane forming tetrafiuoroethylene in situ, is carried out at about 700 C. to about 950 C.
The starting materials for this novel process are halogen-containing organic compounds. Specifically the first member of the mixture is methyl chloride. The second member of a mixture may be either monochlorodifluoromethane or tetrafiuoroethylene. All of these compounds are readily available. A critical feature of the present process is the molar ratio of the two components of the mixture to be pyrolyzed. Where the mixture is made up of methyl chloride and tetrafiuoroethylene, the molar ratio of CF =CF /CH Cl should be about 1:1; the preferred practical range is from 0.8/1 to 1.25/1 moles of tetrafiuoroethylene per mole of methyl chloride. The alternate mixture utilized according to the present invention consists of chlorodifiuoromcthane and methyl chloride and is operable when the molar ratio of CHClF CH Cl is within the range of greater than 1:1 to 2:1, the preferred practical range is 1.6/1 to 2.5/1 moles of chlorodifiuoromethane to methyl chloride; when this molar ratio is greater than 2:1 the effect is one of uneconomical usage of material.
The process of the present invention is carried out by 2.9mm Patented Apr. 5, 1960 continuously introducing the two described components. which make up the mixture, in the vapor phase into a reactor which is inert to the starting materials. The reactor is maintained at a temperature from about 700 C. to about 950 C. The molar ratio of the components of the mixture is maintained as discussed in the previous paragraph. The reactant vapors are then converted to the desired 2,3,3,3-tetrafiuoropropene by pyrolytic action, i.e., by the action of heat. A convenient form of reactor is a metal tube. However, it must be inert to the reactants. Carbon and the noble metals, particularly platinum and silver, are sufficiently inert. A preferred material of construction is a platinum-lined reactor. During the process the reactor tube may be heated by conventional methods. A preferred and convenient way is to place the tube in an electric furnace, which supplies the heat necessary to maintain the reaction temperature. The contact times which are preferred range from 0.5 to 3 seconds. Longer contact times lead to higher molecular weight products instead of the desired 2,3,3,3- tetrafiuoropropene and also tend to carbonize the reactants such as methyl chloride and tetrafiuoroethylene. With shorter contact times, low conversion is obtained. In determining contact times one must consider the volume of the efiiectively heated zone of the reactor, the volume occupied by the reactants at the time they are introduced into the reactor and the rate of feeding the reactants into the reactor. The volume of the effectively heated zone is determined by multiplying the effectively heated length times the cross-sectional area; and the volumes occupied by the reactants are calculated at 25? C. and 760 mm. (Hg) absolute pressure. The contact time will be controlled by the feed rate. After the reaction takes place, the product gases are then collected from the outlet of the reactor tube, cooled, scrubbed with water to remove the acid by-product HCl, and dried. The 2,3,3,3-tetrafluoropropene may be partially separated from the reaction mixture by distillation to yield a product useful for most chemical reactions. Highly purified samples may be obtained either by gas chromatographic separation or by bromination followed by debromination of the purified dibromide. The operable temperature limits have been found to be from about 700 C. to about 950 C. Below 700 C., the conversion is reduced to a point where the process becomes impractical. At about 950 C. and higher, degradation of the reactants and formation of less desirable products occur. The preferred range is 800 to 900 C.
The following representative examples illustrate the novel process of the present invention.
The reactor used in Examples 1 through IV consists of a platinum-lined metal tube 6 mm. ID. x 24 inches heated in an S-inch electric furnace over an efiective reaction length of 5 inches. Analysis of the product gas streams is effected bymeans of mass spectrometry.
. EXAMPLE I Preparation of 2,3,3,3-tetrafluoropropene from CHClF; and CH Cl When a mixture of 2 mols of CHClF and 1 mol of CH Cl at a contact time of 1.0 second is passed through the described reactor at 900 C., there is produced 13.1 mol percent of 2,3,3,3-tetrafluoropropene. At the higher temperature and shorter contact time, approximately the same yield of 2,3,3,3-tetrafluoropropene is obtained as in Example I, but the conversions of CHClF and CH C1 are nearly quantitative.
EXAMPLE III Preparation of 2,3,3,3-tetrafluompropene from tetrafiuoroethylene and methyl chloride A lower contact-time of this Example IV at the same temperature results in an increased yield of 2,3,3,3-tetrafiuoropropene with a lower conversion of CH Cl than in Example III.
EXAMPLE V Preparation "of highly purified 2,3,3,3-'tetfafiuoropropene 'The reactor used consists of a platinum-lined metal tube 6 mm. ID. x 24 inches heated by two 8-inch electric furnaces. the first one serving as a preheater. The effective reaction lengthis -10 inches. Over a period of 220 minutes a mixture of'304 parts (3.04 mols) of tetrafiuoroethylene and 155parts (3.07 mols) of methyl chloride is fed to the reactor. The preheater is maintained at 800 C. and the reactor at-88O C. The contact time is 2.6 seconds. The off gases are scrubbed free of acid by a countercurrent water scrubber, dried, and condensed in a trap cooled to 78 C. This condensate, weighing 242 parts, is distilled using a /2 x 3' silvered column packed with metal packing and a head equipped with magnetic takeoff. The condenser is maintained at 75 C. and the distillation-is performed at a 13/2 reflux ratio. The fractions listed below-are collected.
Fraction B. P., C. Wt. (parts) (The lesson distillation is due to material non-condensable at --78 C.) Fractions I, 11, IV and V are combined and brominated. A bromination apparatus consisting of a gas washing bottle, the inlet tube having a fritted disk, is used; the'calculate'd amount of bromine is placed in thebottleand overlaid with a thin layer of water. The bromine portionis cooled in ice water while a heat lamp isfocused on the bromine-water interface. The olefins are bubbled in at such a rate that nearly complete absorption'occurs. The brominated mixture is then de-colorized with aq. 'Nal-ISO washed with water, and dried over CaCl Distillation of the resulting 130.5 parts of mixed bromidesyields37.4.parts of 2,3-dibromo- 1,1,1,Z-ttrafiuoropfopane, B.P. 98-105" C.
In a 250-ml. 4-necked flask is .placed 77.5 parts of dioxane, 10 parts (0.15 mol) of zinc dust, and 0.1 part of -"Ziuc chloride. "The flask-is equipped with a stirrer,
dropping funnel, thermometer, and a reflux condenser to which is connected a trap cooled in Dry Ice. When the vigorously stirred suspensionfhas been heated to a gentle reflux, a solution of 13.7 parts (0.05 mol) of the above 2,3-dibromo-1,1,1,2-tetrafluoropropane in 15.5 parts of dioxane is added dropwise during 45 minutes in order to effect de-bromination. After the first few parts of solution has been added, a vigorous reaction ensues. The remainder of the addition goes smoothly. Stirring and heating are continued twenty minutes longer. Col lected in the trap is 510 parts of pure liquid product (theory, 5.7 parts). The 2,3,3,3-tetrafluoropropene is identified by its infrared spectrum, C=C at 5.85 and mass spectrum, parent peak at 114, base peak at 69.
The 2,3,3,3-tetrafluoropropene obtained by the process of the present invention has been relatively unavailable to the present time because of the difficulty of preparing the compound. The present novel process therefore yields a heretofore rare but valuable monomer. This monomer may be homopolymerized. The monomer is further useful in that it may be copolymerized with other unsaturated compounds such as tetrafiuoroethylene, trifiuoroethylene, vinylidene fluoride, chlorotrifluoroethylene, acrylonitrile, and '1,1,2-trifluorobutadiene-1,3 to yield plastic or elastomeric polymers.
As many apparently widely diiferent embodiments of this invention may be made without departing from the spirit and scope thereof, it is to be understood that this invention is not limited to the specific embodiments thereof except as defined in the appended claims.
The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
1. A process for preparing 2,3,3,3-tetrafiuoropropene wherein a mixture of about 1 mol of'methyl chloride and a reactant taken from the group consisting of about .1 mol of tetrafiuoroethylene and about 2 moles of'monochlorodifiuoromethane ispyrolyzed, within a contact time range of 0.5 to 3.0 seconds, at a temperature within the range of about 700C. to about 950 C. to'form 2,3,3,3- tetrafiuoropropene which is then recovered from the product stream.
2. A process for preparing 2,3,3,3-tetrafluoropropene wherein a mixture of about 1 mol of methyl chloride and a reactant taken from 'the group consisting of from 0.8 to 1.25 moles of tetrafiuoroethylene and from 1.6 to 2.5 moles of monochlorodifluoromethane is pyrolyzed, within a contact time range of 0.5 to 3'seconds, at a temperature within the range of about 700 C. to about 950 C. to form 2,3,3,3-tctrafluoropropenewhich is then recovered from the product stream.
3. A process for preparing 2,3,3,3-tetrafluoropropene wherein a mixture of about 1 mol of methyl chloride and from 0.8 to 1.25 moles of tetrafiuoroethylene is pyrolyzed, within a contact time range of 0.5 to 3.0 seconds, at a temperature within the range of about 700 C. to about 950 C. to form 2,3,3,3-tetrafiuoropropene which is then recovered from the product stream.
4. A,process for preparing 2,3,3,3-tetrafluoropropene whereina mixture of about .1 mol of methyl chloride and fr0m 1.6 to .25 moles of :monochlorodifiuorornethane is pyrolyzed,-within a contact time range of from 0.5 to 3.0 seconds,=at a temperature within the range of about 700 C. to about 950 C. to form 2,3,3,3-tetrafiuoropropene which-is thenrecoveredirom the product stream.
References 'Citetlin the file of this patent UNITED STATES PATENTS 2,551,573 Downinget a1 May 8, .1951 ..2,733,277 JMiller Ian. 31, .1956 2,758,138 Nelson Aug; 7, 1956 UNITED STATES PATENT OFFICE CERTIFICATION OF CORRECTION Patent No; 2331,8 10 April 5, 1960 David Maley Marquis It is hereby oe'rtified'that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.
Columg 1 line 67 for 12.1" read 1.-6:1
Signed and sealed this 8th day of August 1961.I
(SEAL) Attest:
ERNEST W. SWIDER DAVID L. LADD Attesting Officer Commissioner of Patents

Claims (1)

1. A PROCESS FOR PREPARING 2,333,-TETRAFLUOROPROPENE WHEREIN A MIXTURE OF ABOUT 1 MOL OF METHYL CHLORIDE AND A REACTANT TAKEN FROM THE GROUP CONSISTING OF ABOUT 1 MOL OF TETRAFLUOROETHYLENE AND ABOUT 2 MOLES OF MONOCHLORODIFLUOROMETHANE IS PYROLYZED, WITHIN A CONTACT TIME RANGE OF 0.5 TO 3.0 SECONDS, AT A TEMPERATURE WITHIN THE RANGE OF ABOUT 700*C. TO ABOUT 950*C. TO FORM 2,3,3,3TETRAFLUOROPROPENE WHICH IS THEN RECOVERED FROM THE PRODUCT STREAM.
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US3073870A (en) * 1958-11-25 1963-01-15 Du Pont Process for the pyrolysis of chcif2 and ch3ci to prepare ch2 cf2
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